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Meet The Chicago Woman Arrested 396 Times

A Chicago woman who has been arrested 396 times has become an expert at manipulating the court system—faking seizures so she can stay at hospitals, getting her cases delayed so she can return to the streets and threaten people—all because prisons are overcrowded and mental hospitals are short on funding.

Shermain Miles, 51, has used over 80 aliases since 1978, a period in which she has been arrested 92 times for theft, 65 times for disorderly conduct, 59 times on charges related to prostitution, and five times for robbery or attempted robbery. Although she has been called “acutely psychotic,” she is lucid enough to recognize officers who have previously arrested her when they show up again. When she is arrested, she is generally released without a conviction; she stalls until the victims get frustrated and finally jettison the case. Yet she still has had 73 convictions.

Miles allegedly robbed a 75-year-old Bosnian immigrant, Mujo Cesic, at knifepoint in 2010. He said, “She should never be released.” Miles is in prison in Lincoln, Illinois, which is downstate, jailed because she was allegedly slapping and punching people on a stretch of Broadway in Uptown.

When Miles is free, she won’t sleep in one of Uptown’s estimated 500 shelter beds because she fights with other people in the shelter.

When she is convicted, her sentence is often reduced because of a state law that automatically cuts an inmate’s term in half for many different crimes. Illinois Department of Corrections spokeswoman Stacey Solano explained why she is often arrested without serving jail time: “The Department [of Corrections] makes decisions on a case-by-case basis. And when appropriate, will try to impose community-based sanctions for parolees before [an] automatic return to prison.”

As for mental hospitals, Miles has frequented many, but the results have been nil. Although Thresholds, a North Side agency that says it is the state’s oldest and largest organization for the mentally ill, states, “Within one year of joining a Thresholds program, 90 percent of Thresholds’ members remain out of costly hospital care and nursing home care,” the agency would not discuss Miles, who had been there.

Miles agreed to do an interview with a Chicago Sun-Times reporter, saying, “Since I have gave my life over to the Lord, I have no problem with you coming out here… It is very much appreciated that you are wanting to hear my side of the story.”

When the reporter arrived, Miles asked if she was getting paid. When she was informed she wasn’t, she walked away, saying, “Then I have nothing to say. Jesus already took care of it.”

In Edgewater, where Miles lives, the business community hates the idea of her returning, as she harasses pedestrians and sometimes stands in the middle of the street and stops traffic. Marko Zaric, a spokesman for The Business People for Bryn Mawr, which watches out for crime in the area., said, “There is always one case that rallies a community, and she was that case.”